541513-52-4

Upstream product

• 32233-44-6 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde 
• 67-64-1 acetone 
• 541513-57-9 (4R)-4-benzyl-3-[(2R,3S)-3,5,6-trihydroxy-2-methylhexanoyl]oxazolidin-2-one 
• 101711-78-8 (3R)-3-propionyl-4-benzyloxazolidin-2-one 
• 126946-52-9 ethyl (3S)-3,4-dihydroxy-3,4-O-isopropylidene-butanoate 
• 95422-24-5 methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate 

Downstream Products

• 541513-95-5 (2R,3S,5S)-6-bis(benzyloxy)phosphoryloxy-2-methyl-3,5-bis(tetrahydropyran-2-yloxy)hexanoic acid benzyl ester 
• 541513-79-5 (2R,3S,5S)-3,5-diacetoxy-6-bis(benzyloxy)phosphoryloxy-2-methylhexanoic acid benzyl ester 
• 541513-71-7 (2R,3S,5S)-6-[bis(benzyloxy)phosphoryloxy]-3,5-dihydroxy-2-methylhexanoic acid benzyl ester 
• 541513-63-7 (2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyric acid benzyl ester 
• 541513-67-1 (2R,3S,5S)-3,5,6-trihydroxy-2-methylhexanoic acid benzyl ester 
• 951154-85-1 C₈₀H₁₂₂O₉Si₃ 
• 951154-83-9 13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-ol 
• 672296-47-8 13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3-one 
• 672296-46-7 13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(S),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-4,11,17-trien-3-one 
• 672296-44-5 (2S,4S,5R,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2,4,6,12-tetramethyl-15-trityloxypentadeca-7,13-dien-1-ol 
• 672296-43-4 4(S)-benzyl-3-[9(S),11(S)-bis(tert-butyldimethylsilanyloxy)-5(R)-(4-methoxybenzyloxy)-2(S),4(S),6(S),12(S)-tetramethyl-15-trityloxy-pentadeca-7,13-dienoyl]oxazolidin-2-one 
• 672296-41-2 C₅₇H₈₂O₇Si₂ 
• 672296-42-3 4(S)-benzyl-3-[9(S),11(S)-bis(tert-butyldimethylsilanyloxy)-5(R)-(4-methoxybenzyloxy)-4(S),6(S),12(S)-trimethyl-15-trityloxypentadeca-7,13-dienoyl]oxazolidin-2-one 
• 672296-40-1 (4S,5R,6S,9S,11S,12S)-9,11-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-4,6,12-trimethyl-15-trityloxypentadeca-7,13-dienoic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis and biological evaluation of (-)-dictyostatin and stereoisomers

Total syntheses of (-)-dictyostatin, 6,16-bis-epi-dictyostatin, 6,14,19-tris-epi-dictyostatin, and a number of other isomers and analogs are reported. Three main fragments-top, middle, and bottom-were first assembled and then joined by olefination or anio

ANALOGS OF DISCODERMOLIDE AND DICTYOSTATIN-1, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF

A compound of the following structure: wherein R1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; Ra, Rb and Rc are independently an alkyl group or an aryl group; Rd is an alkyl group, an aryl group, an alkoxylalkyl group, -RiSiRaRbRc or a benzyl group, wherein Ri is an alkylene group; Re is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or -NRgRh, wherein Rg and Rh are independently H, an alkyl group or an aryl group; R3 is (CH2)n where n is and integer in the range of 0 to 5, -CH2CH(CH3)-, -CH=CH-, -CH=C(CH3)-, or -C=-C-; R4 is (CH2)p where p is an integer in the range of 4 to 12, -(CHRkl)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rsl )=C(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1 )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(RsI)CH(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRks)y5C(Rsl)=C(Rs2)CH(Rs3)CH(Rs4)-, -(CHRkI )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rsl)CH(Rs2)CH(Rs3)CH(R s4)-,wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, Rk1, Rk2, Rk3, Rk4 and Rk5 are independently H, CH3, or OR2a, and Rs1,Rs2, Rs3, and Rs4 are independently H or CH3, wherein R2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; and R5 is H or OR2b, wherein R2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; provided that the compound is not dictyostatin 1.

Synthesis of (R)-2-methyl-4-deoxy and (R)-2-methyl-4,5-dideoxy analogues of 6-phosphogluconate as potential inhibitors of 6-phosphogluconate dehydrogenase.

The synthesis of (2R)-2-methyl-4,5-dideoxy and (2R)-2-methyl-4-deoxy analogues of 6-phosphogluconate is described. The synthetic strategy relies on the Evans aldol reaction for the installation of the chiral centres in the 2- and 3-positions. The selective phosphorylation at the primary alcohol function of (2R,3S)-3,6-dihydroxy-2-methylhexanoic acid benzyl ester (5) and (2R,3S,5S)-3,5,6-trihydroxy-2-methylhexanoic acid benzyl ester (20) was achieved with dibenzyl phosphochloridate and dibenzyl phosphoiodinate respectively, working at low temperature. (2R,3S)-3-Hydroxy-2-methyl-6-phosphonoxyhexanoic acid (9) was obtained in 25% overall yield from 4-benzyloxybutanol and (2R,3S,5S)-3,5-dihydroxy-2-methyl-6-phosphonoxyhexanoic acid (28) in 10% overall yield from L-malic acid.